


Press X for Boyfriend

by Talinor



Category: Critical Role (Web Series)
Genre: Dating Sim AU, F/M, Mild CR Spoilers, Modern AU, Mutual Pining
Language: English
Status: Completed
Published: 2019-05-27
Updated: 2019-05-27
Packaged: 2020-03-20 12:24:47
Rating: Teen And Up Audiences
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 2,012
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/18992614
Author URL: https://archiveofourown.org/users/Talinor/pseuds/Talinor
Summary: 'Nearly' was the key word. There was one more member of the Mighty Nein who's romantic route had eluded her so far- Caleb Widogast, a withdrawn wizard who tended to keep to himself and his spellbook. Despite her best efforts to get closer to him, she never seemed to make the right choices to truly woo him. It got to a point where she looked up if he was actually romanceable.He was. It was just a minefield of one wrong choice and it's locked out for the rest of that save nearly the entire time.





	Press X for Boyfriend

**Author's Note:**

> why did I write this? fuck if I know 
> 
> enjoy!

It'd been a pretty boring day for Jessie. All of her friends were busy, any available assignments were already done, and it was only 3 in the afternoon. _Nothing_ was happening online, no matter how many times she refreshed the same three pages.

Needless to say, she was _bored out of her mind._ So she used the only outlet she hadn't tapped into yet: video games.

Now, her library wasn't all that impressive, but she was certain she'd find something to waste a few hours on. She was burned out on Minecraft for now after spending the past couple nights building the most impressive dick-castle known to man, in her own humble opinion. 

The Sims was... pretty tempting. She had quite a couple interesting little saves with their own little dramas. A week or two could _easily_ be sunk into toying with her virtual people. But last time she did that, her friends nearly called the police thinking she was missing. So while it was _very_ tempting, she ultimately decided against it.

The list went on like that for a while. GTA didn't have any interesting new mods, and it wasn't really her kind of game. Overwatch? She had all the arcade lootboxes for the week, plus she didn't want to get yelled at by strangers for the slightest mistake, so that was also a no. Nintendogs? She was too lazy to move her laptop off her lap and get her old WiiU from... wherever it was. Her apartment was a mess. Splatoon? Same problem.

Finally, she remembered an oldie but a goodie: The Misadventures of the Mighty Nein. It was a high fantasy dating sim, but the best one she's ever played. (And she's played _a lot,_ so that was pretty high praise.) Besides the integral dating part, there was a surprising amount of lore behind it. So much so that it was too much to summarize, but it kept her invested in more than just the pretty romance options.

But _hooo boy,_ there were a lot of pretty romance options that she'd nearly finished. Each one had their own unique storyline with different themes behind them. There was even good and bad platonic endings if you for some reason didn't care about getting with anyone, just being good friends with the colorful cast of characters.

There was Fjord, the seafaring half-orc with mysterious connections to an ancient God. His route was high-sea and highkey pretty easy for her to get without looking up the route. There was Beau, a brash human monk trying to improve herself as a person. Her route was simpler, but still very sweet and easy nonetheless. Then there was Mollymauk Tealeaf, a shameless tiefling with a past not even they truly knew. While the others were a soft slow burn, their route was a firecracker of friends-with-benefits to lovers. The only difficult thing about their route was keeping them alive.

But their death not only deepened the other routes emotionally, but opened a new route that was nearly the opposite. Caduceus Clay, a gentle giant of a firbolg, was never interested in the pantsless hokey pokey. But that didn't make his route any less enjoyable. Then there was Nott the Brave, a protective and absolutely _wild_ goblin rogue with a penchant for magic and despising water. Her route only got difficult near the end, trying to stay with her despite the fact she had a halfling husband and son who knew her as Veth. Not only did she manage to stay with Nott, she got a cute little mini-route with her and her husband Yeza as an unconventional but happy family.

The last one she managed to do was the most difficult by far- Yasha, a sweet but standoffish aasimar barbarian with a tendency toward straying from the group. Becoming her friend was no problem, but anything more was quite a struggle. But it was ultimately worth it for her somber storyline about grief and moving on from (but never forgetting) a dead spouse. It was the most beautiful and bittersweet of all the storylines, and she's played nearly all of them.

'Nearly' was the key word. There was one more member of the Mighty Nein who's romantic route had eluded her so far- Caleb Widogast, a withdrawn wizard who tended to keep to himself and his spellbook. Despite her best efforts to get closer to him, she never seemed to make the right choices to truly woo him. It got to a point where she looked up if he was actually romanceable.

He was. It was just a minefield of one wrong choice and it's locked out for the rest of that save nearly the entire time.

She was ready to try and take that challenge again today. She opened the game and started a new save with what had become her signature character- the blue tiefling cleric of a trickster god called the Traveller. Her name was also the same as it always was: Jester Lavorre. The first name was her nickname, the last was given to her by the game. It added a more personal edge to the game she enjoyed.

What would normally be the first hour or so of the game was breezed through in ten minutes. It was basically introductions to most of the characters and how the group gradually forms. While fascinating, she'd been through it enough to know the right choices like the back of her hand.

Part of her was tempted to look up a walkthrough, but she decided against it. She was going to find a way to ignite a fire in the wizard's heart if it took all day and an ungodly amount of reloading saves.

An hour later, she was barely any closer. She'd managed to get a new scene with him, tipsily dancing in a tavern and getting called 'Astrid', but nothing other than that. Asking him about it locked her out of the route. She also flustered him quite a bit with mouth-to-mouth, but that was available in the platonic route too.

So she was in it for the long game and kept on playing... But it didn't feel too different from the platonic route. Was she doing it right? She had no idea. At one point, she wanted to give up entirely.

But then she noticed something. Usually in the big illustrated scenes of her character interacting with the others, Caleb was always looking at a book or his fey familiar Frumpkin. But while nothing else changed about the pictures, Caleb had a different direction to his gaze: her. It was always fond and wistful when no one else was looking to notice.

But _Jessie_ noticed. And, unlike any route beforehand, it actually made her grin and pump her fist in silent victory. Was it sad? Kinda. Did she care? Not really. It had to be the game's subtle encouragement, a small nod meaning _you're still on it, keep going._

The start to chapter 25 was pretty routine. The Mighty Nein were in Rexxentrum, deemed appropriate neutral ambassadors for potential peace talks. They'd just arrived, and while the first meeting was first thing in the morning, the ones who didn't have to do any talking were drinking like _monsters._ Meaning Nott, Beau, and to a lesser degree Yasha.

Caduceus had already helped a tipsy Fjord to his room for the night, so both their route interactions and scenes were closed. Usually Caleb was out first, but he was still in his back corner table this time. That had to mean something, right? 

She cautiously tiptoed around the drinking game scenes with Nott, Beau, or Yasha. She was hoping for something, _anything_ this time. Caleb was from Rexxentrum, though he rarely talked about it and was always tense during visits. He _had_ to have some kind of special scene here. She was sure of it.

Finally she decided to turn in for the night before the bedroom scenes with any of the still-drinking girls. And she struck gold.

 _As you make your way up the stairs,_ the text boxes narrate. She instinctively pressed save. _you're stopped by a hand gently gripping your wrist. You turn around to see it's attached to Caleb, looking up at you with a familiar nostalgic look in his eyes and light flush on his cheeks. He must have been drinking. When he speaks, his voice is hushed._ His sprite appeared above the text boxes. The description was... pretty accurate for the state it showed him in.

 _**Caleb:** "Jester, may I speak to you?" [He pauses for a moment, averting his eyes to glance around before returning them to you.] "...Alone?" _  
> "I'm tired, can we do this in the morning?"  
> "We're alone now."  
> "Are you drunk?"

Okay, it _definitely_ wasn't option number one. But would number two be too much, or would three drive him away somehow? She was flying blind. She had a save ready, but that didn't alleviate her concerns. Finally she did what any rational adult would do with a tough choice: a lightning round of eenie-meenie-miney-mo. Option two was the winner.

_**Caleb:** [He chuckles dryly.] "It looks that way, doesn't it? But things are never as they seem here. There may be prying eyes we're not aware of down here." [He pauses, weighing both of your options. Finally, he speaks again. Louder, like he wants to be heard.] "Let's talk in your room." _

_**Jester:** "'Talk', huh?" _

The sprite's blushing visibly darkened as the text box states, _He doesn't answer, just goes up the stairs towards your room for the night. His hand is still on your wrist. He's not nearly strong enough to pull you along, but do you follow or wrench your wrist out of his grasp?_ That wasn't even a choice for her.

The background changed to a tavern room and the music quieted down to barely audible after the sound of a door creaking shut and locking. Jessie had no idea what was going to happen, but she waited with bated breath. This must be Caleb's bedroom scene. Who knew what it would bring?

His sprite showed up again, looking relieved now. The flush had died down considerably, but it was still there. It was easy enough for her to notice.

_**Caleb:** "There, now we're as alone as we can get in Rexxentrum." [His hand tentatively lets you go.] "Sorry about that. I had to get your attention and I..." [He shakes his head and gets back to business.] "Anyway, you know of Trent Ikithon, ja?" _

Ah, yes. _That_ asshole. He had a pretty minor role in every route, but the dude _radiated_ shadiness. The only reason she went along with him on nearly every route so far was because the alternative was waaaay worse. He was one of those characters that gave off heavy vibes of 'I'm totally gonna betray you at some point' but never did. She liked most of the characters in this game, but not him. Never him.

_**Jester:** "No, why?" _

Oh right. She hadn't met him on this route yet.

 _**Caleb:** "I..." [He sighs, anxiously wringing his hands together. They're shaking.] "I'm sorry, I should..." _  
> "Go on, Caleb. I'm listening."  
> [Let him continue]  
> [Take his hands]

The second one led to him leaving. The third got him a bit farther, but ended the same way. She huffed a bit at that. Fine, then. Guess the first one was the right choice. If it led to him leaving again, she was gonna be _pissed._

_**Caleb:** [He steels himself. His hands still shake, but not as much as before.] "Thank you, blaubeere. There is... no easy way to say this, but you need to know it. I'm tired of hiding it from you." _

_**Jester:** "Yes?" _

Then came the sucker-punch opening line to a backstory reveal. The background darkened around Caleb's deathly serious sprite, and the borders of the text box was lit aflame. 

_**Caleb:** "Let me tell you the story of how I murdered my parents." _

...Oh.

As she read, she grew pissed, but for entirely different reasons.

**Author's Note:**

> please comment! i love little more than seeing 'inbox (1)' or more!  
> my tumblr: squishy--squish   
> my discord: MyBatteryIsLowAndIt'sGettingDark


End file.
